


classy crossdressing shenanigans

by orphan_account



Category: Homestuck
Genre: Crossdressing, M/M
Language: English
Status: Completed
Published: 2011-09-24
Updated: 2011-09-24
Packaged: 2017-10-24 00:08:17
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,256
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/256629
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Done for the (2nd) kinkmeme.</p><p>Original prompt: "john has always been a little curious about wearing girl's clothes, in a sort of derpy "urgh man i'm a little weird aren't i. they're so pretty though!" way.</p><p>dave is only too eager to make it happen."</p>
            </blockquote>





	classy crossdressing shenanigans

John had a secret. He was very careful about it—he hadn't told anyone: not his dad, not his friends. He was pretty sure that his secret was not normal. But, Dave was John's best bro. That's why he knew he could tell Dave anything without having to worry about how Dave would react. Sure, Dave might criticize him a bit, but it would be in his ironic way and John knew that he wouldn't really meant it negatively. Good friends stood by each other no matter what! So, John was pretty sure that he could tell Dave his secret when they were discussing the topic of alchemizing new clothing.

TG: you need some better duds man  
TG: look at me  
TG: suits  
TG: all the way  
TG: cutting imps to ribbons in style  
TG: im like the butcher bridegroom of lohac street  
TG: put on your suit egbert  
TG: its time to dance  
EB: BLUH!! no way! i tried that and it was okay for a while but now i am trying something new! that is just too cool for me, i guess. i think clothing should be comfortable!!  
TG: no  
TG: it should be awesome  
TG: or ironic I guess  
TG: but you dont really get irony so thats not an option  
EB: but isn't it good to have your own style?  
EB: you should try different stuff and maybe you will like it.  
EB: i think you should alchemize casual clothing!!  
TG: i already did that  
TG: and then i switched to suits  
TG: besides i am not taking fashion advice from a kid in a lab coat  
EB: :P  
EB: i'm not wearing a lab coat anymore!  
EB: but i guess i do have some weird ideas about clothing  
TG: what  
EB: i mean i always sort of wondered what it would be like wearing girl's clothing  
EB: it's all so pretty!!  
EB: i've never done it because i don't think my dad would have been okay with it  
EB: dave?  
EB: are you still there?  
EB: you're taking awhile to respond  
TG: sorry I had to do something  
TG: dont worry about it its not even a thing  
TG: so you want to wear girls clothing  
TG: thats cool bro  
EB: i'm glad! i was worried you might be weirded out!!  
EB: i should have known my best bro would support me! :)  
TG: ok  
TG: egbert  
TG: im gonna give you a captchalog code  
TG: use it  
TG: or not  
TG: i mean i really dont care  
TG: but  
TG: i might stop by lowas soon  
TG: maybe  
TG: you never know

 

Dave sent John a code and refused to say what it was for before logging off Pesterchum. It was all a bit suspicious but there were a lot of things Dave did that John did not understand, so he was not really worried. John used the code and went about the process of making a cruxite totem and alchemizing the item, which turned out to be... “The THREE IN THE MORNING DRESS?” While this was very nice of Dave, and John saw this as a very friendly gesture in accepting his quirks, John could not help but feel that the dress was not really his style.

John glanced around his living room. There had to be something that he could combine with this to make it better. He decided to try out random things and hope for the best. Either way, alchemizing things was fun!

Remembering his WISE GUY SLIME SUIT, he combined the code of the dress with the code of his copy of WISE GUY. He got the GAMBLER GIRL GETUP, which was a better color in John's opinion, but looked a bit uncomfortable.

On a whim, he combined it with his PROBLEM SLEUTH game. The result was the SCALE BODICE which, for some reason, was much too small. It looked more like something a doll would wear. He decided not to worry about it, and moved on, looking for other items.

He tried again, combining the THREE IN THE MORNING DRESS with a HARLEQUIN DOLL (because why not?) and creating the MIDNIGHT ARLECCINA DRESS. Oh my. It was, well, it certainly looked comfortable. And also frilly and pretty and John really, really wanted to try it on. He glanced around nervously, as if he could sense the eyes of a troll watching him at this moment in his timeline if he simply looked hard enough. He scurried inside his house to his room. Trashed by imps or not, he felt safer here. Sending up a quick prayer to gog that Rose was not watching him at that moment, John undressed and put on the MIDNIGHT ARLECCHINA DRESS.

The dress was soft and lightweight. It was vividly colored, with diamonds the color of pool balls running up the entire length. It came with white stockings and black shoes, and poofy white bloomers that John blushed about, but put on anyway. John glanced around guiltily. He was probably enjoying wearing the dress too much. He could just hear the lecture he would get from Karkat if he happened to see him like this. Remarkably, he didn't hear any dings to signify he was being pestered (or trolled) on Pesterchum.

Instead, he heard a knock on his bedroom door.

John walked over to the door nervously. Imps didn't knock, so it had to be a person. He really hoped it wasn't Rose. She would never let the psychoanalysis end. He opened the door a crack and peeked through. “Oh, Dave! Hey, you actually came by,” John opened the door all the way and took a few steps back to let Dave into the room. After all, Dave was probably expecting to see him wearing a dress, so it didn't matter if he saw John now. “Thanks for the code for the dress! I ended up combining it with a few things to see what I'd get and I really liked this one.” John turned on the spot to show of his handiwork, enjoying the way the movement made the skirt flutter around his legs.

Dave Strider had come by expecting to see John in a long, dark green dress. He had prepared himself for the sight, and had assured himself that he could play it cool around John long enough to imprint the image forcefully in his mind for later reviewing. He had not expected to see John derping around in a short dress and white stockings that ended suggestively mid-thigh. But it was cool. No big deal. Dave was chill as the fucking polar ice caps.

And that explained why he suddenly strode forward and grabbed John's shoulders. Irony, man. Learn it.

“Dave? Uh, is there something wrong?” John grinned a goofy, bucktoothed, nervous little grin, like he wasn't quite sure what Dave was doing but he wasn't all that worried.

Dave felt his pulse quicken. John was too trusting. Too easy to take advantage of. He needed someone to protect him, a valiant Knight to guard his honor, to save him from the impudent advances of...oh, screw it. Dave leaned forward and caught John in a kiss.

John opened his mouth in shock, and stumbled backwards a bit. Dave took advantage of this and followed John back while deepening the kiss. He walked John unsteadily across the room until they met with the bed, which John fell back upon, breaking the kiss. Dave crawled up on the bed to kneel over John, panting. “Egbert, what the fuck.”

John sat up, supporting himself with his arms as he leaned back a bit. “Uh, I think that's what I'm supposed to say. This is unexpected, Dave!”

Dave scoffed. “I come in here and find you in this frilly little dress and you expect me not to do this? It's like an invitation, bro, fancy script and everything, 'you're invited to attend a private showing of John Egbert's legs!' I think I'm obligated to accept.” He sat back and put his hands on John's thighs, just above where the stockings ended.

John blushed vibrantly and clenched the sheets beneath him. “D-dave! I'm not sure I'm comfortable with, um, all of this. I mean, I don't like guys.”

“Egbert. Shut up. You're so deep in the closet you're chilling with the boogeyman.” Dave considered his options: stockings on or off? He rubbed John's thighs as he tried to imagine both possibilities.

“I am not! I like girls,” John tried to look offended, but it ended up looking more like he was pouting.

Dave noted that John didn't look uncomfortable, and wasn't trying to shove Dave off of him. “You mean you like dressing like girls. It's not the same thing, I thought you understood that,” he smirked. Yes, stockings on would definitely be the better choice. John looked like he was about to come up with a retort, but Dave's hands slid up John's legs, and one hand cupped the bulge in the little bloomers.

“Ahh!” John's arms gave out, and he fell back onto the bed. “Dave! What do you—nngh!”

Dave had reached inside the bloomers and taken John's dick. He pumped John lightly, enjoying the way John's breath was coming in short little gasps. Dave slid his hand down further, fondling John's balls while stroking the apex of John's thigh with his thumb. After a minute he let go in favor of pulling the bloomers down John's legs just enough to expose him completely. He observed his work.

John was breathing shakily, hands clenched, knuckles white, eyes teary behind glasses. He looked up at Dave, unsure but needy, an unspoken request on his slightly parted lips.

Fuck. To hell with being calm and collected, Dave had needs. He palmed his crotch before unzipping his pants and putting out his own cock, which was already fully erect. “Goddammit, Egbert. Why do you have to look so fucking tempting?”

John offered up a shaky smile. “I promise, it's not intentional!” He tried to pull himself out from underneath Dave, suddenly more nervous at seeing Dave's arousal. “I mean, I was just going to put on the dress and maybe wear it for a little bit, but then you came over and when you started kissing me it was sort of okay but I'm not really even into those things and—ack!”

Dave pulled John back by his legs and sat down on them, holding John in place. “Ok Egbert, listen up. Rule one, you are banned from speaking. Rule two, you are going to lie there and deal with it,” he leaned forward and initiated another kiss. John was completely still at first, but he hesitantly opened his mouth (after Dave's tongue had prodded his lips insistently enough). Dave's tongue slid against John's trying to encourage his to be an active participant. Ever so slowly, John responded.

John was not a very good kisser, but his reaction gave Dave some encouragement—he hadn't been totally sure of John's compliance in all of this, and he really didn't want to force his best friend into something he would hate him for later. Dave pulled away and nuzzled into John's neck, mouthing just under his jawline. “God, John,” he thrust his hips forward, rubbing his aching cock against John's.

The Heir of Breath cried out breathlessly, and Dave almost commented on the irony. He repeated the motion, and was rewarded with a similarly attractive noise coming from John's mouth.

“Dammit, Egbert,” he huffed into John's ear, continuing to grind against him, “When we beat this fucking game, you're going to have to wear dresses more often.”

John's arms reached around Dave's neck and flailed, trying to find something to hold on to. “Dave! Ohgod, I've never—” His nails dug into Dave's shoulders as he clutched Dave to him tightly, and whined.

Dave chuckled, still smug despite the situation, “Never what? Bumped dicks with another dude? No problem, bro.” He managed to sound cocky, though not quite as composed as he usually did.

“N-no, I mean,” John moaned, “not even by myself.”

Had it been any other situation, Dave might have frozen in shock. But he sure as hell wasn't going to stop moving, even for such an admission. “Fuck, seriously?” No wonder he was in denial.

“Yeah,” John turned his head and breathed the word into Dave's neck, making Dave's neck hairs stand up.

Dave smiled broadly into the crook of John's neck, getting an idea. “Never jerked it to the thought of someone before?”

“Wha? Dave, no—”

Dave pressed his lips to John's ear. “Never reached down and touched yourself, imagining someone else's hands?” He slipped one of his hands down between them and grasped both his and John's hard-ons, stopping his thrusting in favor of pumping his hand.

“Ohh, god, what are you—”

Dave started to thrust into his hand, even as he continued to pump himself and John. “Never dreamed about getting fucked and woken up covered in your own cum?”

“Dave! I—I think I'm—!”

“Come, John,” Dave whispered in John's ear.

John came with a high wail, and Dave followed soon after. Dave sat up after a few minutes of breathing heavily, collapsed on top of John. John was laying spread-eagle on the bed, eyes closed and panting. The skirt to his dress was bunched up around his waist and splattered with semen. He opened his eyes and turned his head to look up at Dave, face flushed.

Dave smirked. “Congratulations, Egbert. Now you're a man.”

**Author's Note:**

> This is bad and I should feel bad. Protip: I do.


End file.
